6-azido-6-deoxy-D-glucitol | 906341-00-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-azido-6-deoxy-D-glucitol
• 英文别名: (2S,3R,4R,5R)-6-azidohexane-1,2,3,4,5-pentol
• CAS: 906341-00-2
• 化学式: C₆H₁₃N₃O₅
• 分子量: 207.186
• InChiKey: BPWHMSFNUDJDKX-JGWLITMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.27
• 重原子数：
  14.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  149.91
• 氢给体数：
  5.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-azido-6-deoxy-D-glucitol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以95%的产率得到6-amino-6-deoxy-D-glucitol
  参考文献：
  名称：

  The direct synthesis of 6-amino-6-deoxyaldonic acids as monomers for the preparation of polyhydroxylated nylon 6

  摘要：

  6-Azido-6-deoxy-D-galactitol and D-mannitol were obtained quantitatively via the reduction of the corresponding 6-azido-6deoxy-D-hexono-1,4-lactones, and 6-azido-6-deoxy-D-glucitol was obtained by the reduction of 6-azido-6-deoxyglucose in good yields. The reduction of monoazidodeoxyhexitols by catalytic hydrogenation gave the monoaminohexitol analogues in 95-98% yields. Oxidation of these afforded the corresponding 6-amino-6-deoxy-D-aldonic acids in moderate yields. Alternatively, saponification of 6-azido-6-deoxy-D-hexonolactones gave 6-azido-6-deoxyaldonic acid salts which, after reduction followed by neutralization, led to the expected compounds in 82-88% overall yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.04.018
• 作为产物：
  描述：

  D-葡萄糖 在 sodium tetrahydroborate 、 叠氮化锂 、 四溴化碳 、 三苯基膦 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 6-azido-6-deoxy-D-glucitol
  参考文献：
  名称：

  The direct synthesis of 6-amino-6-deoxyaldonic acids as monomers for the preparation of polyhydroxylated nylon 6

  摘要：

  6-Azido-6-deoxy-D-galactitol and D-mannitol were obtained quantitatively via the reduction of the corresponding 6-azido-6deoxy-D-hexono-1,4-lactones, and 6-azido-6-deoxy-D-glucitol was obtained by the reduction of 6-azido-6-deoxyglucose in good yields. The reduction of monoazidodeoxyhexitols by catalytic hydrogenation gave the monoaminohexitol analogues in 95-98% yields. Oxidation of these afforded the corresponding 6-amino-6-deoxy-D-aldonic acids in moderate yields. Alternatively, saponification of 6-azido-6-deoxy-D-hexonolactones gave 6-azido-6-deoxyaldonic acid salts which, after reduction followed by neutralization, led to the expected compounds in 82-88% overall yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.04.018